These are the questions we ponder as the top balladeer of the early '90s turns 60 on February 26. Back in his heyday, there were tens of thousands of hair-metal singers... but only one hair-adult-contemporary star, which made him the closest thing the pop world had to a Fabio doppelgänger. Hard as it is to believe, it's been 16 years since he underwent a severe scissoring. To put it in perspective, he's spent about two and a half times as long with short hair as he ever spent in the limelight as a long-tressed superstar.

But even with a newly published memoir, The Soul Of It All, that delves into his romances with such starlets as Ashley Judd, Teri Hatcher, and Nicolette Sheridan, all anyone interviewing him wants to know is: Does he regret the dated signature hairstyle, and/or the loss of it?

"It was really traumatic," he said last month, asked once again to recall the fateful year of 1997. "It was like a part of my childhood and my rebellion and everything I went through to wear long hair... It became my look. Not exaggerating, there was probably a good $50 million to $100 million in marketing that was spent establishing my appearance all over the world.”

A mane that mighty should have taken Paul Bunyan's axe to chop off—not just the mere cutlery of stylist-to-the-stars Chris McMillan, whose most famous work besides shearing Bolton was creating "the Rachel" for Jennifer Aniston.

"I had no idea it would be such a big deal. I remember I was in London and I was watching some serious news story, when they interrupted the bulletin with, ‘News just in–Michael Bolton cuts his hair!’ It was hysterical. But we raised about $9,000 for women and children at risk, so it was worth it."

A mere $9K? It sounds like Bolton entrusted them to the wrong auctioneer. Peter Morton could have opened a whole chain of Adult Contemporary Cafes by parceling out all those inches of curls to different franchisees.

Bolton's career trajectory would seem to provide evidence that Samson syndrome is not just the stuff of myth. Consider this: In the years 1990-97, Bolton was an international superstar who sold more than 24 million albums in the United States alone. But after he got his news-shattering haircut, 1997's All That Matters became his first album since 1985 not to go platinum; 1998's My Secret Passion became the first since '85 not to reach the top 100 in sales; and 1999's Timeless: The Classics Vol. 2 became the first since then not to reach the top 200, even though it was the sequel to an album that had reached No. 1 and sold 4 million copies just seven years earlier.

But at least his girlfriend at the time liked it. Or did she? Back in late '97, he was dating Judd, of whom he then said: "Ashley was the first person to say that she actually kind of missed my long hair. I went back to the studio after I got the haircut... I was definitely insecure about it, I felt kind of naked without it... Fortunately for me... people were coming in to look at me and they were being extremely complimentary. And at one point, I was sure my assistant had either cajoled them or paid them to boost my morale." Ominously, perhaps, he and Judd broke up almost immediately afterward.

It definitely didn't hurt him with all the ladies, anyway, as he and Sheridan went on to have an engaged-again, not-engaged-again romance that ended for a second time in the late 2000s. And then there was his destined-to-be-career-reviving appearance on Dancing With the Stars. Well, make that his blink-and-you'll-miss-it appearance.

In the season that featured such brilliant hoofers as Bristol Palin, Bolton was the second to be eliminated, trailing only first-off David Hasselhoff in the rush to be thrown off. He got into a public war of words with judge Bruno Tonioli after being eviscerated for his lack of dancing chops on the air. "I think this is probably the worst jive in 11 seasons," Tonioli told him in front of the cameras, the night before he was voted off. Bolton demanded satisfaction: "I think he should apologize publicly and he should be reprimanded for it," he said after leaving the show.

Then there was the Office Space notoriety, with the 1999 Mike Judge comedy that had a character ruing having the same name as the "no-talent ass-clown." It wasn't easy to tell if Bolton—the real-life Bolton—had a sense of humor about this. Asked if he had a defense against the comedic digs, he said, "Well, no, just Grammys and awards given by my peers... I have signed so many Office Space DVDs, and I have it, but I've never seen it. From what I've heard, they should do an Office Space 2, and I should meet Michael Bolton in it."

But things turned around in a big way in 2011 when he got in on the joke, or at least in on a joke. Andy Samberg and his Lonely Planet cohorts enlisted Bolton to star in a Saturday Night Live video for a song called "Jack Sparrow," in which, for no logical reason, the singer kept interrupting their hip-hop bravado with hooks explaining his incongruous love of all things Pirates of the Caribbean.

At first Bolton was worried that the clip would be too raunchy for his fans. Then one of his daughters assured him it would be a social-media phenomenon, and he saw the light—which, let's face it, is easier without 18-inch bangs. How much did he get into it? In his autobiography, which starts out with a chapter about the experience, he writes, "I think all three of them [in the Lonely Planet] were shocked when I agreed to a traumatizing scene in which I dressed as Erin Brockovich and breast-fed a doll. Unfortunately, that scene didn’t make the cut."

Even without a breastfeeding scene, "Jack Sparrow" was a major hit. Since debuting on SNL, it's racked up more than 102 million views on YouTube. Who needs a mullet when you're No. 1 on YouTube with a bullet?

Suddenly, the idea of Michael Bolton, Comedy Star is weirdly taking hold. ABC has a sit-com in development called Michael Bolton's Daughter is Destroying My Life, in which he is set to play a "caricaturized" version of himself. "If they like what they read, we shoot the pilot in the spring," he said last month. "If they like the pilot, I'm on the air in the fall. And it's hysterical... I'm like a 12 year old [in mentality]. So [I find] this girl, this young 24, 25-year-old journalist who's really well grounded... and I bring her in and I want her to be the bridge in this relationship between me and my daughter. She accepts the job, realizing after the first day that she's going to have to babysit for both my daughter and me."

In real life, he became a grandpa in 2010 when his daughter Taryn gave birth to a baby girl. Of being called Grandpa, he said, “I’m going to have to figure out how to own that.”

As for whether he's owning being 60: He'll be on stage at the Strand Theatre in York, Pennsylvania, and says "there is nothing I would rather be doing than performing" as he celebrates—or avoids?—the big day.

And regrets? He's had a few, but not the trail of tresses down his back. "I don’t cringe when I look back at that look, that hair, because it a huge was part of my 20 plus years of 'overnight success' and who I was as an individual and as an artist," he told Pennlive.com this week. Anyway, it all comes back in the end. Or on the sides. "I cut my hair off and sold it for charity but now I have hair growing out of my ears," he said in 2010. "I don't know if it's revenge or something."

Credit him with some foresight for ditching the hairstyle in his 40s, anyway: As he creeps into his 60s and 70s, any temptation to do a comb-over will be entirely absent.